Ok -- a SPECIFIC bar idea since you are still are talking to her and learning your role as lover/friend/minder/chaperone person. Just idea -- tailor it for you if you like it.
"Winging it" with no plan is not safe to me. "Have safety word plan in place" to enable one to take risk in sane way is safer to me.
If you are out together and she wants to pick someone up? She gives you the paper with her name/number/hotel key and YOU deliver it to the person and say "My friend, the lady at table ____ wants me to give you this with her compliments. If you would like me to introduce you, I'd be happy to walk you over."
Person up for it and intrigued, you escort X to her table.
"M, here is X. How about some drink/snack?" Make chit chat for 10 min in trio or so. End with "Smile for camera bday girl!" (take pix of them on cel phone.)
Then say "You guys seem cozy so I am going to bow out and let you two get acquainted on your own and take in some sights myself. M, call me in an hour to check in. Have fun you guys!"
M can explain who you are to the degree she's happy with -- he's my friend, this is my bday vacation, etc.
You disappear to where you and M agreed you would be "on call." Your hotel room, hotel lobby, whatever. Don't drink booze if you are on chaperone duty, do your JOB. When it is your night for wild oats she is the chaperone she can return the favor then.
That let's X know you have your "safe word stuff" in place with M, and if X pulls a creeper you will be raising hell and setting the police on X's ass like white on rice with full name, handy recent photo of last location seen. Hell, take a pix of the license.
A pix of ID and pix with bday girl is
cheap admission into her hotel room for sex adventures. Best turf is her turf -- her hotel room. Hotels don't have guns, knives, other people in the closet to rape you gang bang style, etc. Then you can be in YOUR hotel room -- best next door. Or in lobby. Handy.
If she's decided to hook up and leaves the location to do it, X knows she's gonna be calling to check in with you first to tell you where she is and when the NEXT check in call will be happening. M can let X know to expect her to call post sex to check in with you -- her safe word person. Still up for sex fun -- yay. Not? Shoo.
No creeper with a brain and unhealthy boundaries is gonna pull a stunt with a chaperone around WITH a picture, expecting check in calls. X doesn't need to know you have hotel room next door. Creepers dont' like "hassles" -- nobody gets raped on supermarket produce stands. The goal is to put enough hoops to weed out the crazies, but not so many it spoils the fun or makes it unsafe.
Decide the safe words for
- Doing (w)ell. no probs-- ("Having a (W)oNDERFUL time! Check in soon!") "well" = "wonderful" W's.
- HELP! (G)et me out. ("Having a (G)REAT time! Check in soon!") get me out = "great" G's.
That's your cue to make up shit and say you are glad she called because you are drunk and are lost in town, are in the hospital, lalala so she can go "OH CRAP! My friend! I am so sorry -- let's do this tomorrow ok? I need to get him. And LEAVE with x none the wiser. Solve tomorrow tomorrow. Get tonight solved NOW.
Any adventurous polysexual person with a brain and healthy boundaries will recognize "a clean, healthy hook up" and praise the heavens for sane hook up people to hook up with with "safe word" manners.
It is possible to have fun sowing wild oats with some precaution and style/manners.
My 2 cents.
Galagirl